Toluene → 3-(Pyrimidin-2-yl)benzaldehyde

HRID 990423Notes

Reaction equation

HRID 990423 reaction equation
C1(C)C=CC=CC=1.Cl[C:9]1[N:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[CH:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)=[O:16].C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CN(C=O)C>[N:10]1[CH:11]=[CH:12][CH:13]=[N:14][C:9]=1[C:21]1[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH:15]=[O:16]

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 27343563-Formylphenylboronic acid

Product 1

HCID 226308183-(Pyrimidin-2-yl)benzaldehydeYield 39.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EX-603A) To a toluene (15 mL) solution of 2-chloropyrimidine (1.00 g, 8.7 mmol) was added 3-formylphenylboronic acid (1.42 g, 9.5 mmol) and DMF (8 mL). To the resulting solution was added K2CO3 (2.63 g, 19.0 mmol) and Pd(PPh3)4 (0.52 g, 0.45 mmol). The slurry was heated to reflux under argon for 18 h. The cooled mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane gave 0.63 g (39%) of the desired 3-(2-pyrimidinyl)benzaldehyde product as a brown oil which solidified upon standing. MS: m/z=185.1 [M+H]+.

Workup

  1. temperatureThe slurry was heated
  2. temperatureto reflux under argon for 18 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil
  7. customPurification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-434e0452fd4a42e8897ded7a21d688e1
Source dataset
uspto-grants-2002_10
Patent number
US06458803B1

Reaction notes

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